Iranian chemical communication

Organic chemistry

Synthesis, characterization and polymerization of a novel acrylate monomer containing both 4H-pyran-4-one and 1,2,3-triazole moiety and evaluation of their antibacterial activity

Mahnaz Saraei; Gholamreza Zarrini; Parisa Rajabpour

Volume 6, Issue 3, pp. 218-324, Serial No. 20 , July 2018, , Pages 271-279

Abstract

  A novel acrylate monomer containing 4H-pyran-4-one and 1,2,3-triazole ring, {1-[4-(4-oxo-6-phenyl-4H-pyran-2-yl)benzyl]-1,2,3-triazol-4-yl}methyl acrylate was synthesized by the reaction of 2-{4-[(4-(hydroxymethyl)-1,2,3-triazol-1-yl)methyl]phenyl}-6-phenyl-4H-pyran-4-one with acryloyl chloride in the ...  Read More A novel acrylate monomer containing 4H-pyran-4-one and 1,2,3-triazole ring, {1-[4-(4-oxo-6-phenyl-4H-pyran-2-yl)benzyl]-1,2,3-triazol-4-yl}methyl acrylate was synthesized by the reaction of 2-{4-[(4-(hydroxymethyl)-1,2,3-triazol-1-yl)methyl]phenyl}-6-phenyl-4H-pyran-4-one with acryloyl chloride in the presence of triethylamine. The structure of the acrylate monomer was established on the basis of FT-IR, 1H NMR, 13C NMR, MS and elemental analysis. This monomer was polymerized using 2,2´-azobisisobutyronitrile (AIBN) as the initiator in N,N-dimethylformamide solution. Thermal stability of the polymer was investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The synthesized compounds were evaluated for their antibacterial activity against Gram-positive and Gram-negative bacteria using the disk diffusion method. The results of antibacterial assay indicated that these compounds exhibited moderate bactericidal activity.

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Organic chemistry

Facile and convenient synthesis of 2-amino-5,10-dioxo-4-aryl-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile derivatives by electrocatalytically chemical transformation

Zahra Vafajoo; Davood Kordestani; Saba Vafajoo

Volume 6, Issue 3, pp. 218-324, Serial No. 20 , July 2018, , Pages 293-299

Abstract

  2-Amino-5,10-dioxo-4-aryl-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile derivatives are obtained in excellent yields with a simple and efficient procedure.This reaction can occur using electrocatalytic multicomponent chain transformation of aryl aldehydes, 2-hydroxynaphthalene-1,4-dione and malononitrile ...  Read More 2-Amino-5,10-dioxo-4-aryl-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile derivatives are obtained in excellent yields with a simple and efficient procedure.This reaction can occur using electrocatalytic multicomponent chain transformation of aryl aldehydes, 2-hydroxynaphthalene-1,4-dione and malononitrile under neutral and mild conditions. Moreover, electrolysis is done in CH3CN as solvent, Tetrabutylammonium fluoride (TBAF) as an effective supporting electrolyte and an iron electrode as the cathode and a graphite electrode as the anode in undivided cell. Also Excellent conversions of the starting materials were obtained under 10 mA/cm2 current densities after 0.54 F/mol of electricity had been passed and I=50 mA at room temperature. The key advantages of this method are the high yields, simple work up the non-chromatographic purification of products.

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Organic chemistry

Ultrasound assisted oxidation of various alcohols to corresponding aldehydes by using Al2O3 as catalyst

Sadegh Rahmati; Ardeshir Khazaei; Maryam Golbaghi; Mohammad Panahimehr

Volume 6, Issue 2, pp. 109-217, Serial No. 19 , April 2018, , Pages 109-113

Abstract

  A convenient approach for oxidation of structurally diverse alcohols has been developed using KMnO4 as oxidant agent in the presence of a catalytic amount of Al2O3 in aqueous acetonitrile. In this method various alcohols generally afforded the corresponding carbonyl compounds directly in good to high ...  Read More A convenient approach for oxidation of structurally diverse alcohols has been developed using KMnO4 as oxidant agent in the presence of a catalytic amount of Al2O3 in aqueous acetonitrile. In this method various alcohols generally afforded the corresponding carbonyl compounds directly in good to high yield under ultrasound irradiation conditions. It shows that this kind of catalysis system is very active, selective and suitable for oxidation of benzylic alcohols. Furthermore, all products were obtained through a simple filtration and washed with solvent, and there was no need for column chromatography. All products have been characterized by IR and 1HNMR spectral data.

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Organic chemistry

Petra, osiris and molinspiration: A computational bioinformatic platform for experimental in vitro antibacterial activity of annulated uracil derivatives

Ajmal R Bhat

Volume 6, Issue 2, pp. 109-217, Serial No. 19 , April 2018, , Pages 114-124

Abstract

  Annulated pyrano[2,3-d]pyrimidine/pyrano[2,3-d]uracil derivatives were synthesized using aromatic aldehydes, active methylene compounds and barbituric acid in presence of dibutylamine (DBA) catalyst in ethanol as solvent. The different substituents on phenyl ring in the fused pyrano uracil skeleton showed ...  Read More Annulated pyrano[2,3-d]pyrimidine/pyrano[2,3-d]uracil derivatives were synthesized using aromatic aldehydes, active methylene compounds and barbituric acid in presence of dibutylamine (DBA) catalyst in ethanol as solvent. The different substituents on phenyl ring in the fused pyrano uracil skeleton showed productive influence on its antimicrobial activity against some gram positive and gram negative bacteria like Pseudomonas aureus, E. coli, Staphylococcus aureus, Klebsiella pneumonia and Bacillus cereus. Antibacterial screening revealed that the presence of heteroaryl, cyano and amino groups on uracil skeleton increases its penetrating power on bacterial cell wall and product becomes more biologically energetic. The antimicrobial activity results showed some definite and interesting facts about the structure activity relationship (SAR) of synthesized molecules.

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Organic chemistry

Efficient one-pot synthesis of 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates catalyzed by nano MgO in water

Maryam Sojoudi; Masoud Mokhtary

Volume 6, Issue 2, pp. 109-217, Serial No. 19 , April 2018, , Pages 125-133

Abstract

  Water is a versatile solvent in many ways, and in this sense performing organic reactions in this medium is now of great interest. The one-pot reaction of ethyl acetoacetate or benzyl acetoacetate, with benzaldehydes and malononitrile to provide some novel 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates ...  Read More Water is a versatile solvent in many ways, and in this sense performing organic reactions in this medium is now of great interest. The one-pot reaction of ethyl acetoacetate or benzyl acetoacetate, with benzaldehydes and malononitrile to provide some novel 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates has been performed over nano MgO with high performance in water as a green solvent at 80 °C. The nanocrystalline MgO catalyst was characterized via X-ray diffraction (XRD), transmission electron microscopy (TEM) and BET analysis. This method offers considerable improvements for the synthesis of 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates with concern to the yield of products, facility in operation, and green aspects without using of toxic catalysts and solvents.

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Organic chemistry

One-pot multicomponent click synthesis of some novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes

Mosadegh Keshavarz

Volume 6, Issue 2, pp. 109-217, Serial No. 19 , April 2018, , Pages 134-142

Abstract

  A facile and one-pot multicomponent synthesis of novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes at room temperature is reported. At the first step, in the presence of I2/NaN3 reagents, various alkenes were converted to the corresponding azido iodides and in the next step, the reaction of these ...  Read More A facile and one-pot multicomponent synthesis of novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes at room temperature is reported. At the first step, in the presence of I2/NaN3 reagents, various alkenes were converted to the corresponding azido iodides and in the next step, the reaction of these compounds with phenylacetylene in the presence of catalytic amount of sodium ascorbate/ CuSO4 afforded regioselective synthesis of 1,4-disubstituted-1H-1,2,3-triazoles in short times and at good to high yields. This greenapproach has several advantages such as short reaction times, clean reaction profiles, and simple experimental and workupprocedures. All the products were fully characterized by 1HNMR, 13CNMR, IR and CHN analysis

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Organic chemistry

Isolation and identification macrocyclic spermine alkaloid(protoverbine) from verbascum speciosum.

Majid Halimi; Malihe Nasrabadi

Volume 6, Issue 2, pp. 109-217, Serial No. 19 , April 2018, , Pages 143-147

Abstract

  The 17-membered macrocyclic spermine alkaloid protoverbine (8-phenyl-1,5,9,13-tetra azacycloheptadecan-6-one) was isolated From the aerial part of verbascum speciosum. The natural polyamines are ubiquitous bases reported to have several important functions in animals, plants and microorganisms. They ...  Read More The 17-membered macrocyclic spermine alkaloid protoverbine (8-phenyl-1,5,9,13-tetra azacycloheptadecan-6-one) was isolated From the aerial part of verbascum speciosum. The natural polyamines are ubiquitous bases reported to have several important functions in animals, plants and microorganisms. They are involved in processes of transcription and translation in protein synthesis and influence growth and development (cell division, differentiation, embryogenensis, etc.). In plants their involvement in organ development, flowering, fruit ripening, senescence and stress responses is reported. The structure of the protoverbine established by a study of their spectral such as 1HNMR,13C-NMR, IR, ESI-MS analyses and chemical properties. To the best of our knowledge, this is the first report of protoverbine from this species.

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Organic chemistry

The zinc chromium ferrite magnetic nanoparticles ZnCrFeO4: An efficient catalyst for acetylation of alcohols, phenols and amines under solvent-free conditions

Nahid Rasouli; Maryam Movahedi; Elaheh Aghabeikzadeh Naeini

Volume 6, Issue 2, pp. 109-217, Serial No. 19 , April 2018, , Pages 169-179

Abstract

  In this study, the zinc chromium ferrite magnetic nanoparticles ZnCrFeO4 are synthesized via sol-gel method and characterized by X-ray diffraction (XRD) analysis, Fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM). The XRD analysis showed that ZnCrFeO4 has single-phase ...  Read More In this study, the zinc chromium ferrite magnetic nanoparticles ZnCrFeO4 are synthesized via sol-gel method and characterized by X-ray diffraction (XRD) analysis, Fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM). The XRD analysis showed that ZnCrFeO4 has single-phase cubic structure. The synthesized ZnCrFeO4 has been used as an efficient catalyst for acetylation of alcohols, phenols and amines with acetic anhydride under mild and solvent free conditions. The ZnCrFeO4 catalyst can be readily removed using an external magnet and no obvious loss of activity was observed after three consecutive runs. Also, the effect of time, amount and type of catalyst were investigated.

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Organic chemistry

Mn (III) salen complex supported on graphene oxide nanosheets as a highly selective and recoverable catalyst for the oxidation of sulfides

Ali Allahresani

Volume 6, Issue 2, pp. 109-217, Serial No. 19 , April 2018, , Pages 180-191

Abstract

  In this study, Mn (III) salen complex was synthesized and immobilized onto the graphene oxide, which is modified by 3-chloropropyltrimethoxy silane. Heterogeneous catalyst was characterized by X-ray diffraction, transmission electron microscopy, thermogravimetric analysis, fourier transform infrared ...  Read More In this study, Mn (III) salen complex was synthesized and immobilized onto the graphene oxide, which is modified by 3-chloropropyltrimethoxy silane. Heterogeneous catalyst was characterized by X-ray diffraction, transmission electron microscopy, thermogravimetric analysis, fourier transform infrared spectra, nitrogen adsorption−desorption isotherm and atomic absorption spectroscopy. The catalytic activity of heterogeneous Mn (III) salen complex and comparison with its homogeneous analogue was studied for green oxidation of sulfide derivatives using aqueous 30% H2O2 as an oxidant in water media. The results showed that heterogeneous catalyst was highly efficient in this reaction and corresponding products were obtained in good to excellent yields. The advantages of this catalyst include short reaction times, no side reactions, easy and simple work up, mild reaction conditions and excellent selectivity. The heterogeneous nanocatalyst was reused for several runs without significant loss in activity and selectivity.

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Organic chemistry

Design, preparation and characterization of a novel BiFeO3/CuWO4 heterojunction catalyst for one-pot synthesis of trisubstituted imidazoles

Hamed Ramezanalizadeh

Volume 6, Issue 2, pp. 109-217, Serial No. 19 , April 2018, , Pages 192-208

Abstract

  In this work a novel heterojunction catalyst have been synthesized and employed as a highly efficient catalyst for one-pot synthesis of substituted imidazoles. Analytical methods including Fourier transform infrared (FT-IR), diffuse reflectance spectroscopy (DRS), X-ray diffraction (XRD), Energy- dispersive ...  Read More In this work a novel heterojunction catalyst have been synthesized and employed as a highly efficient catalyst for one-pot synthesis of substituted imidazoles. Analytical methods including Fourier transform infrared (FT-IR), diffuse reflectance spectroscopy (DRS), X-ray diffraction (XRD), Energy- dispersive X-ray spectroscopy (EDX), Scanning electron microscopy (SEM) and Vibrating Sample Magnometer (VSM) were used for the catalyst characterization. Moreover, the catalyst was also recovered and reused five times without remarkable decrease in its catalytic activity. Compared to the classical methodologies, this method illustrated significant advantages including low loading of the catalyst, short reaction times, high to excellent yields, easy separation and purification of the products.

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Organic chemistry

Nickel ferrite as a recyclable nanocatalyst for synthesis of novel highly substituted 1,4-dihydropyrano[2,3-c]pyrazole derivatives

Mohammad Reza Poor Heravi; Naheed Morsalie

Volume 6, Issue 1, pp. 1-108, Serial No. 18 , January 2018, , Pages 87-96

Abstract

  Highly substituted 1,4-dihydropyrano[2,3-c]pyrazole derivatives were synthesized by four-component reaction of aromatic aldehydes, malononitrile, ethyl acetoacetate and various phenylhydrazine, using nickel ferrite as a recyclable nanocatalyst by a grinding method under solvent-free and thermal conditions. ...  Read More Highly substituted 1,4-dihydropyrano[2,3-c]pyrazole derivatives were synthesized by four-component reaction of aromatic aldehydes, malononitrile, ethyl acetoacetate and various phenylhydrazine, using nickel ferrite as a recyclable nanocatalyst by a grinding method under solvent-free and thermal conditions. The reaction has the advantages of good yields, less pollution, ease of separation of the desired products, and of being environment friendly. A possible mechanism for this reaction was proposed. Highly substituted 1,4-dihydropyrano[2,3-c]pyrazole derivatives were synthesized by four-component reaction of aromatic aldehydes, malononitrile, ethyl acetoacetate and various phenylhydrazine, using nickel ferrite as a recyclable nanocatalyst by a grinding method under solvent-free and thermal conditions. The reaction has the advantages of good yields, less pollution, ease of separation of the desired products, and of being environment friendly. A possible mechanism for this reaction was proposed.

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Organic chemistry

One-pot, organocatalytic synthesis of spirooxindoles using citric acid in aqueous media

Zahed Karimi-Jaberi; Abdolhossein Fereydoonnezhad

Volume 5, Issue 4, pp. 364-493, Serial No. 17 , October 2017, , Pages 407-416

Abstract

  Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications.The development of multicomponent reactions designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal ...  Read More Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications.The development of multicomponent reactions designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. in this Manuscript, a facile and efficient multicomponent synthesis of functionalized spirooxindoles has been described through the reaction of isatin, malononitrile or ethyl cyanoacetate, and CH- acids (1,3-dicarbonyl compounds) in the presence of catalytic amount of citric acid in excellent yields with short reaction times in aqueous ethanol. Also citric acid catalyzed synthesis of 3,3-diindolyl oxindoles by the condensation of isatin with substituted indoles.

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Organic chemistry

Green and efficient synthesis of functionalized 3-amino-2-oxofuranes using trityl chloride

Seyed Sajad Sajadikhah; Mahboubeh Zarei

Volume 5, Issue 4, pp. 364-493, Serial No. 17 , October 2017, , Pages 436-441

Abstract

  Extremely facile and efficient procedure has been developed for the synthesis of alkyl 2,5-dihydro-2-oxo-5-aryl-3-(arylamino) furan-4-carboxylate in the presence of trityl chloride (TrCl) as an organic catalyst in ethanol at ambient temperature. One-pot three-component reaction of aromatic amines, dimethyl ...  Read More Extremely facile and efficient procedure has been developed for the synthesis of alkyl 2,5-dihydro-2-oxo-5-aryl-3-(arylamino) furan-4-carboxylate in the presence of trityl chloride (TrCl) as an organic catalyst in ethanol at ambient temperature. One-pot three-component reaction of aromatic amines, dimethyl and/or diethyl acetylenedicarboxylates and aryl aldehydes offorded the corossponding 3-amino-2-oxofurane derivatives in good to high yields. The presented method offers several advantages such as green and mild conditions, simplicity of operation, non-toxicity of the catalyst and high atom economy. Moreover, the products were obtained through simple filtering and no need to column chromatography, which reduces the waste as well as environmental pollutions.

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Organic chemistry

Cu(II)-Schiff base/SBA-15 as an efficient catalyst for synthesis of chromeno [4′,3′-b]pyrano[6,5-b]quinoline derivatives

Radineh Motamedi; Ghasem Rezanejade Bardajee; Somaye Shakeri

Volume 5, Issue 4, pp. 364-493, Serial No. 17 , October 2017, , Pages 442-448

Abstract

  Some chromeno[4′,3′-b]pyrano[6,5-b]quinoline derivatives were synthesized by condensation of 2-amino-4-aryl-3-cyano-5-oxo-4H, 5H -pyrano-[3,2-c] chromenes and 1,3-cyclohexanedione in an environmentally benign and efficient method by Cu(II)-Schiff base/SBA-15 as an environmentally friendly ...  Read More Some chromeno[4′,3′-b]pyrano[6,5-b]quinoline derivatives were synthesized by condensation of 2-amino-4-aryl-3-cyano-5-oxo-4H, 5H -pyrano-[3,2-c] chromenes and 1,3-cyclohexanedione in an environmentally benign and efficient method by Cu(II)-Schiff base/SBA-15 as an environmentally friendly heterogeneous and recyclable catalyst under solvent-free conditions in high yields and rates. These kinds of catalysts are built from mesoporous silica SBA-15 which was covalently anchored with Cu(II) Schiff base complex. The shorter reaction times, good yields, simple work-up procedure and environmentally friendly conditions are the main advantages of this method compared to the last one. The product was identified by its 1H NMR, mass and IR spectra, which were compared to those reported previously.

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Organic chemistry

Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate

Ali Ramazani; Masoome Sheikhi Sheikhi; Ali Souldozi; Sang Woo Joo; Hooriye Yahyaei

Volume 5, Issue 4, pp. 364-493, Serial No. 17 , October 2017, , Pages 449-470

Abstract

  Dimethyl (z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butenedioate has been synthesized using one-pot three component reaction between N-isocyaniminotriphenylphosphorane (Ph3PNNC), 3-methylcyclopentene-1,2-dione and dimethyl acetylenedicarboxylate. Also, optimized geometry and nuclear magnetic resonance ...  Read More Dimethyl (z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butenedioate has been synthesized using one-pot three component reaction between N-isocyaniminotriphenylphosphorane (Ph3PNNC), 3-methylcyclopentene-1,2-dione and dimethyl acetylenedicarboxylate. Also, optimized geometry and nuclear magnetic resonance ( NMR ) of the title compound are evaluated using HF and B3LYP methods and 6-311+G(d) basis set. Moreover, the 1H and 13C NMR chemical shift values of the molecule are calculated and compared with experimental results. Frontier molecular orbitals (FMOs), total density of states (DOS), electronic properties, natural charges, NMR parameters and NBO analysis for product were calculated by theoretical calculations. Finally, molecular electrostatic potential (MEP) surface is obtained for understanding the active regions of molecule.

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Organic chemistry

Silica bonded n-propyl-1,3,5-triazine-2,4,6-triamine as a basic catalyst for synthesis of arylmethylenemalononitrile and pyran annulated heterocyclic compounds

Jamal Davarpanah; Afzal Zafarpour; Behrooz Tayebi

Volume 5, Issue 4, pp. 364-493, Serial No. 17 , October 2017, , Pages 471-483

Abstract

  In the present research, silica bonded n-propyl-1,3,5-triazine-2,4,6-triamine (SPTT) was synthesized by direct incorporation of chloropropyl groups through co-condensation of tetraethyl orthosilicate (TEOS) and 3-chloropropyl trimethoxysilane (CPTMS) and subsequent grafting the melamine onto the propyl ...  Read More In the present research, silica bonded n-propyl-1,3,5-triazine-2,4,6-triamine (SPTT) was synthesized by direct incorporation of chloropropyl groups through co-condensation of tetraethyl orthosilicate (TEOS) and 3-chloropropyl trimethoxysilane (CPTMS) and subsequent grafting the melamine onto the propyl groups via simple nucleophilic substitution reaction. The catalyst has been characterized by fourier transform infrared spectroscopy (FT-IR) and thermogravimetric analysis (TGA). The catalytic activity of catalyst was probed through synthesis of arylmethylenemalononitrile and pyran annulated heterocyclic compounds.The catalytic activity of catalyst was probed through synthesis of arylmethylenemalononitrile and pyran annulated heterocyclic compounds.The catalytic activity of catalyst was probed through synthesis of arylmethylenemalononitrile and pyran annulated heterocyclic compounds.

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Organic chemistry

Fe3O4@SiO2-SO3H as a recyclable heterogeneous nanomagnetic catalyst for the one-pot synthesis of substituted quinolines via Friedländer heteroannulation under solvent-free conditions

Monire Beyki; Mehdi Fallah-Mehrjardi

Volume 5, Issue 4, pp. 364-493, Serial No. 17 , October 2017, , Pages 484-493

Abstract

  An efficient method has been developed for the Friedländer synthesis of substituted quinolines through a condensation reaction of 2-aminoaryl ketones with α-methylene ketones in the presence of a catalytic amount of nano Fe3O4@SiO2-SO3H under solvent-free conditions at 110 °C. The reactions ...  Read More An efficient method has been developed for the Friedländer synthesis of substituted quinolines through a condensation reaction of 2-aminoaryl ketones with α-methylene ketones in the presence of a catalytic amount of nano Fe3O4@SiO2-SO3H under solvent-free conditions at 110 °C. The reactions are completed in short times, and the products are obtained in good to excellent yields. The results revealed several advantages to our procedure, including high product yields, short reaction time, facile work-up procedure, simplicity in operation, eco-friendly reaction conditions, reusability of the catalyst and green aspects by avoiding toxic catalysts and solvents. The catalyst could simply be separated and recovered from the reaction mixture by an external magnet and reused in subsequent reactions without significant loss in activity.

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Organic chemistry

Benign synthesis of N-aryl-3,10-dihydroacridin-1(2H)-one derivatives via ZnO nanoparticle-catalyzed Knoevenagel condensation/intramolecular enamination reaction

Hamid Saeidian; Farzaneh Moradnia

Volume 5, Issue 3, pp. 237-363, Serial No. 16 , July 2017, , Pages 252-261

Abstract

  An efficient construction of 2-(N-arylamino)benzaldehydes and N-aryl-3,10-dihydroacridin-1(2H)-one derivatives starting from 2- hydroxybenzaldehydes has been developed. The synthesis of N-aryl-3,10-dihydroacridin-1(2H)-ones is based on the Knoevenagel condensation of dimedone to various 2-(N-arylamino)benzaldehydes, ...  Read More An efficient construction of 2-(N-arylamino)benzaldehydes and N-aryl-3,10-dihydroacridin-1(2H)-one derivatives starting from 2- hydroxybenzaldehydes has been developed. The synthesis of N-aryl-3,10-dihydroacridin-1(2H)-ones is based on the Knoevenagel condensation of dimedone to various 2-(N-arylamino)benzaldehydes, followed by an intramolecular enamination in the presence of 20 mol% of nanocrystalline ZnO. Moderate to high yields, operation simplicity, and cheap starting materials are the key features of the present method. The structures of the products were confirmed by 1H and 13C NMR spectroscopy and mass spectrometry (EI). Probable mechanisms for the present reactions to account for the formation of 2-(N-arylamino)benzaldehydes 3a-h and N-aryl-3,10-dihydroacridin-1(2H)-one derivatives 4a-h are also reported.

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Organic chemistry

A green synthesis of functionalized thiazol-2(3H)-imine via a three-component tandem reaction in ionic liquid media

Ashraf Sadat Shahvelayati; Leila Hajiaghababaei; Akram Panahi Sarmad

Volume 5, Issue 3, pp. 237-363, Serial No. 16 , July 2017, , Pages 262-267

Abstract

  In this research, an efficient synthesis toward 2-(2-((4-Methoxybenzoyl)imino)-4-(4-methoxyphenyl)thiazol-3(2H)-yl)-2-phenylacetic acid via a three-component tandem reaction using aroylisothiocyanate, phenyl glycine, and 4-methoxyphenacyl bromide in an ionic liquid (IL) has been described. 1-Methyl-3-pentylimidazolium ...  Read More In this research, an efficient synthesis toward 2-(2-((4-Methoxybenzoyl)imino)-4-(4-methoxyphenyl)thiazol-3(2H)-yl)-2-phenylacetic acid via a three-component tandem reaction using aroylisothiocyanate, phenyl glycine, and 4-methoxyphenacyl bromide in an ionic liquid (IL) has been described. 1-Methyl-3-pentylimidazolium bromide (IL) has been employed as a recyclable green solvent. The work-up procedure was fairly simple and the product did not require further purification. The influence of various reaction parameters such as solvent, temperature, and time was examined and among the various solvents such as ethanol, acetonitrile, n-hexane, water, and ionic liquid for synthesis of the final product, the best result was obtained in 1-methyl-3-pentylimidazolium bromide at 50oC for 1 hours.

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Organic chemistry

N-methyl pyridinium-p-toluene Sulfonate (NMPyTs) catalyzed synthesis of pyrano[2,3-c]pyrazoles

DR. Vinod T. Kamble; Dr. Giribala Bondle; Dr. Sandeep T Atkore

Volume 5, Issue 3, pp. 237-363, Serial No. 16 , July 2017, , Pages 268-277

Abstract

  Abstarct:A simple one-pot synthesis of pyrano[ 2,3-c]pyrazoles was developed by a three-component reaction of various benzaldehydes, malononitrile and 1-phenyl or hydro-3-methyl-1H-pyrazol-5(4H)-one in the presence of N-methyl pyridinium p-toluene sulfonate (NMPyTs) as a catalyst. All of the synthesized ...  Read More Abstarct:A simple one-pot synthesis of pyrano[ 2,3-c]pyrazoles was developed by a three-component reaction of various benzaldehydes, malononitrile and 1-phenyl or hydro-3-methyl-1H-pyrazol-5(4H)-one in the presence of N-methyl pyridinium p-toluene sulfonate (NMPyTs) as a catalyst. All of the synthesized compounds were identified by IR, 1H NMR, 13C NMR and mass spectroscopy techniques. In the mentioned method, the use of thermal condition is avoided. The key advantages of this process are high yields, shorter reaction times, easy work-up, and purification of products by the non-chromatographic method. The synthesis of pyrano[2,3-c] pyrazoles using NMPyTs as an efficient catalyst is the novel methodology work.

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Organic chemistry

Separation identification and antioxidant evaluation of zingiber officinale essential oil

Ali Saberi; Mehri Alimohammadi

Volume 5, Issue 3, pp. 237-363, Serial No. 16 , July 2017, , Pages 278-285

Abstract

  Usage of herbal medicine has been under so much attention for many years. They are gradually replacing synthetic drugs in pharmaceutical fields due to their fewer side effects. Nowadays, essential oils are widely used for the treatment of diseases as well as being applied as pesticide. In this study, ...  Read More Usage of herbal medicine has been under so much attention for many years. They are gradually replacing synthetic drugs in pharmaceutical fields due to their fewer side effects. Nowadays, essential oils are widely used for the treatment of diseases as well as being applied as pesticide. In this study, 32 components of Zingiber essential oil were identified representing 97.42% of the extracted oil by Gas chromatography-mass spectrometry (GC/MS). Antioxidant activity of the extracted oil were evaluated. In this experiment the effect of Zingiber essential oil on oxidation temperature of oleic acid was investigated by using a diffential scanning calorimetric (DSC) instrument.

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Organic chemistry

LaCl3.7H20: An efficient catalyst for one-pot multi-component synthesis of 1,4-polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction

Abhijeet Somwanshi; Yashwant Bhaskar Pandit; Akash Gholap; Rushikesh Ghogare; Shivaji Pandit

Volume 5, Issue 3, pp. 237-363, Serial No. 16 , July 2017, , Pages 293-300

Abstract

  An efficient one pot multi component synthesis of 1, 4-Polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction using lanthanum chloride heptahydrate (LaCl3.7H2O) from an aromatic aldehyde, ethyl acetoacetate, dimedone and ammonium acetate as a nitrogen precursor in ethanol at room temperature ...  Read More An efficient one pot multi component synthesis of 1, 4-Polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction using lanthanum chloride heptahydrate (LaCl3.7H2O) from an aromatic aldehyde, ethyl acetoacetate, dimedone and ammonium acetate as a nitrogen precursor in ethanol at room temperature is described. In the present work we report lanthanum chloride heptahydrate remarkably non-toxic in nature and ease of handling we explored the utility of lanthanum chloride as a catalyst for the synthesis of 1, 4-polyhydroquinoline derivatives. We newly report p-N, N-dimethylamino-cinnamaldehyde and m-chlorobenzaldehyde for the synthesis of 1, 4-Polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction and was characterized by IR and 1HNMR spectroscopic methods.

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Organic chemistry

1,3-Dichloro-5,5-dimethyl hydantoin and Poly N,N′-dibromo-N-ethyl naphthyl-2,7-disulfonamide as efficient catalysts for the methoxymethylation of alcohols under solvent-free conditions

Abbas Amini Manesh; Ardeshir Khazaei; Maedeh Gohari; Mahdieh Chegeni; Shahnaz Saednia

Volume 5, Issue 3, pp. 237-363, Serial No. 16 , July 2017, , Pages 308-314

Abstract

  Methoxymethylation of a variety of alcohols was performed using formaldehyde dimethyl acetal in the presence of 1,3-dichloro-5,5-dimethyl hydantoin [DCDMH] and Poly N,N′-dibromo-N-ethyl naphthyl-2,7-disulfonamide [PBNS] as catalysts at room temperature and under solvent-free conditions. Our experiments ...  Read More Methoxymethylation of a variety of alcohols was performed using formaldehyde dimethyl acetal in the presence of 1,3-dichloro-5,5-dimethyl hydantoin [DCDMH] and Poly N,N′-dibromo-N-ethyl naphthyl-2,7-disulfonamide [PBNS] as catalysts at room temperature and under solvent-free conditions. Our experiments show that primary and secondary alcohols can be smoothly converted into the corresponding MOM-ethers in excellent yields. The methoxymethyl ethers (MOM-ethers) were obtained with good to excellent yields. 1,3-Dichloro-5,5-dimethyl hydantoin [DCDMH] and Poly N,N′-dibromo-N-ethyl naphthyl-2,7-disulfonamide [PBNS] effectively catalyzed the methoxymethylation of alcohols with dimethoxymethane at ambient temperature. The notable advantages of this method are mild reaction conditions, high yields, cheapness, safety and eco-friendliness, and recyclability of the catalysts.

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Organic chemistry

H3PW12O40 as an efficient catalyst for one-pot- tricomponent synthesis of chromeno[4,3-b]quinolones under microwave irradiation

Radineh Motamedi; Sara Sobhani; Farshid Barani

Volume 5, Issue 3, pp. 237-363, Serial No. 16 , July 2017, , Pages 338-344

Abstract

  Some Chromeno[4,3-b]quinoline derivatives were synthesized in a tricomponents one-pot reaction of 1,3-cyclohexadione arylaldehydes and 4-aminocoumarin under Microwave irradiation in the solventless system by using a heteropolyacid catalyst ,H3[PW12O40] in 80-95% yields and high rates. The shorter reaction ...  Read More Some Chromeno[4,3-b]quinoline derivatives were synthesized in a tricomponents one-pot reaction of 1,3-cyclohexadione arylaldehydes and 4-aminocoumarin under Microwave irradiation in the solventless system by using a heteropolyacid catalyst ,H3[PW12O40] in 80-95% yields and high rates. The shorter reaction times, one-pot, good yields, simple work-up procedure and environmentally friendly conditions are the main advantages of this method compared to the two step method. Heteropolyacid is separated by filtration and the products were purified by flash column chromatography. The reactions were monitored by TLC and subsequent work-up afforded a single compound by TLC in each case. The product was identified by its 1H NMR, mass and IR spectra, which were compared to those reported previously.

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Organic chemistry

Reusable Silica supported Perchloric acid and potassium bisulphate as green catalysts for thiocyanation of aromatic compounds under solvent free conditions

Chinna Rajanna Kamatala; Hemanth Sriram Y.; Satish Kumar Mukka; Venkateswarlu Marri; Touheeth Fatima; Sai Sudhakar Mukka; Madhusudan Raju R.

Volume 5, Issue 3, pp. 237-363, Serial No. 16 , July 2017, , Pages 352-363

Abstract

  Reusable silica supported perchloric acid and potassium bisulphate have been prepared and explored as green catalysts for thiocyanation of aromatic compounds under conventional and solvent free microwave assisted conditions. The microwave assisted protocol exhibited remarkable rate accelerations and ...  Read More Reusable silica supported perchloric acid and potassium bisulphate have been prepared and explored as green catalysts for thiocyanation of aromatic compounds under conventional and solvent free microwave assisted conditions. The microwave assisted protocol exhibited remarkable rate accelerations and offered selective thiocyanation of aromatic and hetero aromatic compounds in good yields. Reaction times observed in conventional methods range of 2.0 to 6.0 hours, which reduced to only few minutes (1 to 3 min) in microwave assisted reactions. The developed protocols are also promising and comparable with the existing procedures. Prepared catalysts could be easily recycled for five time with a reproducible efficiency.

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